Skip to main content

Advertisement

Log in

New gold carbene complexes as candidate anticancer agents

  • Published:
BioMetals Aims and scope Submit manuscript

Abstract

Three structurally related gold(I) carbene complexes with bulky hydrophobic ligands i.e. 13 were investigated in solution for further consideration as candidate anticancer agents. Cytotoxic assays were subsequently conducted on bone marrow-derived preosteoclast cell line of human origin (FLG 29.1) and human colon cancer cells (HCT-116). A far greater cytotoxic activity was measured for compound 1 against HCT-116 cells compared to 2 and 3; conversely, all compounds were highly and similarly active against FLG 29.1 cells. Results obtained for the reaction of complexes 1 and 2 with RNase A documented the occurrence of a weak interaction with this model protein and the formation of a tiny amount of the corresponding adduct. Moreover, a certain reactivity of the complex 2 was also detected toward GSH. The general implications of the obtained results are discussed.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6

Similar content being viewed by others

References

  • Bertrand B, Casini A (2014) A golden future in medicinal inorganic chemistry: the promise of anticancer gold organometallic compounds. Dalton Trans 43:4209–4219

    Article  CAS  PubMed  Google Scholar 

  • Bertrand C, Citta A, Franken IL, Picquet M, Folda A, Scalcon V, Rigobello M, Pia L, Gendre P, Casini A, Bodio E (2015) Gold(I) NHC-based homo- and heterobimetallic complexes: synthesis, characterization and evaluation as potential anticancer agents. J Biol Inorg Chem 20:1005–1020

    Article  CAS  PubMed  Google Scholar 

  • Chowdhury SK, Katta V, Beavis RC, Chait BT (1990) Origin and removal of adducts (molecular mass = 98 u) attached to peptide and protein ions in electrospray ionization mass spectra. J Am Soc Mass Spectrom 1:382–388

    Article  CAS  PubMed  Google Scholar 

  • Đurović MD, Bugarčić ZD, Rominger F, Puchta R, Van Eldik R (2016) Studies on the reactivity and redox stability of gold(I/III)-carbene complexes. Unexpected inertness of a gold(I)-bis-carbene complex. Dalton Trans (submitted)

  • Garner ME, Niu W, Chen X, Ghiviriga I, Abboud KA, Tan W, Veige AS (2015) N-heterocyclic carbene gold(I) and silver(I) complexes bearing functional groups for bio-conjugation. Dalton Trans 44:1914–1923

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  • Hashmi ASK, Lothschütz C, Graf K, Häffner T, Schuster A, Rominger F (2011) A short way to switchable carbenes. Adv Synth Catal 353:1407–1412

    Article  CAS  Google Scholar 

  • Jones G, Lautner J (1988) Chloro(dimethyl sulfide)gold(I). Acta Cryst 44:2089–2091

    Google Scholar 

  • Lin IJB, Vasam CS (2007) Preparation and application of N-heterocyclic carbene complexes of Ag(I). Coord Chem Rev 251:642–670

    Article  CAS  Google Scholar 

  • Nobili S, Mini E, Landini I, Gabbiani C, Casini A, Messori L (2010) Gold compounds as anticancer agents: chemistry, cellular pharmacology, and preclinical studies. Med Res Rev 30:550–580

    CAS  PubMed  Google Scholar 

  • Öfele K (1968) 1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer übergangsmetall-carben-komplex. J Organomet Chem 12:42–43

    Article  Google Scholar 

  • Pratesi A, Gabbiani C, Michelucci E, Ginanneschi M, Papini AM, Rubbiani R, Ott I, Messori L (2014) Insights on the mechanism of thioredoxin reductase inhibition by gold N-heterocyclic carbene compounds using the synthetic linear selenocysteine containing C-terminal peptide hTrxR(488–499): an ESI-MS investigation. J Inorg Biochem 136:161–169

    Article  CAS  PubMed  Google Scholar 

  • Ray S, Mohan R, Singh JK, Samantaray MK, Shaikh MM, Panda D, Ghosh P (2007) Anticancer and antimicrobial metallopharmaceutical agents based on palladium, gold, and silver N-heterocyclic carbene complexes. J Am Chem Soc 129:15042–15053

    Article  CAS  PubMed  Google Scholar 

  • Wanzlick HW, Schönherr HJ (1968) Direct Synthesis of a Mercury Salt-Carbene Complex. Angew Chem Int Ed Engl 7:141–142

    Article  CAS  Google Scholar 

Download references

Acknowledgments

AP, DC and LM gratefully acknowledge the financial support from Beneficentia Stiftung (Vaduz, Liechtenstein), Ente Cassa di Risparmio di Firenze and AIRC (IG-16049). MDD and ZDB acknowledge the Ministry of Education, Science and Technological Development Serbia, project No. 172011. MDD acknowledge the research grant from the Deutscher Akademischer Austauschdienst (DAAD), Germany.

Author information

Authors and Affiliations

Authors

Corresponding authors

Correspondence to Živadin D. Bugarčić or Luigi Messori.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Pratesi, A., Cirri, D., Đurović, M.D. et al. New gold carbene complexes as candidate anticancer agents. Biometals 29, 905–911 (2016). https://doi.org/10.1007/s10534-016-9962-0

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10534-016-9962-0

Keywords

Navigation